反应详情

温度

-78 °C

To a solution of methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (198.0 mg) in tetrahydrofuran (3.96 ml) was added dropwise a solution of n-butyl lithium (0.634 ml of 1.51 M solution in hexane) at -78° C. over a period of 5 minutes. After stirring for 15 minutes at -78° C., the reaction mixture was added with a solution of acetone (0.0713 ml) in tetrahydrofuran (0.642 ml) at -78° C. over a period of 5 minutes. After stirring for 25 minutes at -78° C., the reaction mixture was added dropwise with a solution of benzyl chloroformate (0.1274 ml) in tetrahydrofuran (1.15 ml) at -78° C. over a period of 5 minutes. The resulting solution was allowed to warm to 0° C. over a period of 40 minutes and added with acetic acid (0.0639 ml) at 0° C. The solvent was distilled off in vacuo at 0° C. and the residue was dissolved in ethyl acetate (30 ml) and washed with brine, aqueous sodium bicarbonate, brine, and saturated aqueous sodium chloride. After drying over magnesium sulfate, the ethyl acetate extract was filtered and evaporated in vacuo. The residual oil (381.2 mg) was chromatographed on silica gel (11 g) eluting with a mixture of ethyl acetate and hexane (1:10→1:5) to give methyl 2-[(3R,4R)-3-(1-benzyloxycarbonyloxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (221.2 mg) as an oil.

1. stirringAfter stirring for 25 minutes at -78° C.
2. temperatureto warm to 0° C. over a period of 40 minutes
3. distillationThe solvent was distilled off in vacuo at 0° C.
4. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
5. washwashed with brine, aqueous sodium bicarbonate, brine, and saturated aqueous sodium chloride
6. dry with materialAfter drying over magnesium sulfate
7. extractionthe ethyl acetate extract
8. filtrationwas filtered
9. customevaporated in vacuo
10. customThe residual oil (381.2 mg) was chromatographed on silica gel (11 g)
11. washeluting with a mixture of ethyl acetate and hexane (1:10→1:5)